


More Than Detention

by Taybay14



Series: Saving people, writing prompts [24]
Category: Supernatural
Genre: 2nd chapter established bdsm relationship, Aftercare, Alternate Universe, Alternate Universe - BDSM, Alternate Universe - High School, Begging, Bondage, Bottom Dean Winchester, Cas uses a belt on Dean, Cuddles, Dean Is A Good Boy, Dean Winchester Has Self-Worth Issues, Dean Winchester Has a Crush on Castiel, Dom Castiel/Sub Dean Winchester, Dom/sub, Edging, Face-Fucking, Feelings, Gentle Dom Castiel (Supernatural), Good Boy, Happy, Light BDSM, Orgasm Delay/Denial, Panties-Wearing Dean Winchester, Porn With Plot, Praise, Praise Kink, Prostate Stimulation, Rebel Dean Winchester, Reward, Riding Crops, Safewords, School Principal Castiel (Supernatural), Slight Breath Play, Smut, Spanking, Sub Dean, Subspace, Teacher Castiel (Supernatural), Teacher-Student Relationship, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester, Toys, Trust Issues, blowjob, dean is 18, heart to heart, non-verbal safeword, playroom, sleepover, testing soft limits
Language: English
Status: Completed
Published: 2019-07-04
Updated: 2019-08-22
Packaged: 2020-06-03 19:08:12
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 11,893
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19470280
Author URL: https://archiveofourown.org/users/Taybay14/pseuds/Taybay14
Summary: Tumblr Prompt fill:Azh-vanquisher-queen:  #19. “Do you care to explain why you’ve been sent to my office three times this week?”------Castiel turns him so he's facing the desk, then rests his lips against the shell of Dean's ear. He chuckles when the boy shudders and presses back against him. "I think you're in need of something much more hands on than detention, don't you think Mr. Winchester?"Dean frantically nods, looking over his shoulder at Castiel with wide green eyes."I think naughty boys like you need a lesson."-----Chapter Two now added since so many of you requested one!! Enjoy (:





	1. Chapter 1

**Author's Note:**

> *** basic premise: Dean’s the rebel at his school (18 yo) and Castiel is the new straight laced principal that thinks he can wrangle him warning: not underage because Dean’s 18, but it’s still a teacher/student situation so if that makes you uncomfortable then don’t read it.

“Dean Winchester?” Dean lifts his head halfway, eyes remaining on the book he’s reading. It’s the only acknowledgement he gives the secretary that he heard her. “Mr. Novak will see you now.”

“Yeah, I bet he will,” Dean says with a smirk. He stands up and walks past her without another word, knowing the way to the new principal’s office extremely well. Before he enters the room, Dean slips his small paperback copy of Allen Ginsberg’s _Howl_ into the back pocket of his jeans. It’s the only thing he changes. He leaves the half-smoked cigarette tucked behind his ear. He doesn't remove his leather jacket, or the flask of his dad's whiskey that's resting in one of the pockets. He definitely doesn't zip that jacket closed, even if his cotton white shirt is so thin you can see every tattoo beneath it. 

Dean doesn't knock, instead just pushing into the office. Mr. Novak isn't even surprised anymore at the behavior. He just stares blankly at Dean as the young man closes the door, locks it, and slumps down in a chair on the opposite side if Mr. Novak's desk. 

"Mr. Winchester," the principal finally states as a way of greeting.

Dean nods his head. "Novak."

"What is it this time? Smoking in the bathroom? Having sex in the janitor's closet? Sneaking-"

"Blowjob," Dean states simply, interrupting him.

"What?"

"The incident you're referring to. From last week." Dean winks at him. "It was a blowjob in the janitor's closet. Not sex."

"Same thing, Winchester."

"Actually, Novak, it's not." Dean rests his elbows on his knees and leans forward, grinning. "Want me to show you?"

As always, Mr. Novak isn't flustered. He just continues to look at Dean with contempt. After a few more seconds of staring each other down, Mr. Novak sighs. 

"Do you care to explain why you've been sent to my office three times this week?"

"No problem, teach. Let's see," Dean tilts his chin and looks at the ceiling like he's thinking hard. "Well, first was the fire alarm issue. Second, if I remember correctly, was for telling Mr. Singer that he's a pompous ass who-"

"Language," Mr. Novak says in a tired, uncaring voice. 

Dean doesn't miss a beat. "Believes that no one can have an opinion on the material but him. As if he was there when Vonnegut fucking wrote-"

"Language."

"Slaughterhouse Five. You think that prissy dick has ever-"

"Language."

"Stepped foot in war? Or in any situation that left him traumatized? I sincerely fucking doubt-"

"Language."

"It, Mr. Novak." Dean shrugs and sits back, not even winded from his angry rant. His body is used to them. "Three, however, is my favorite."

Mr. Novak arches an eyebrow. "Getting caught skinny dipping in the school pool in the middle of the school day is your favorite?"

Dean winks at him, smiling wide. "See, I knew you were aware of why I was here."

"Mr. Winchester, you -"

"Call me Dean."

"Excuse me?"

Dean leans forward again, darting his tongue out to wet his lips. "You'll be seein' a lot of me, handsome. Might as well call me Dean. It's shorter. Easier. Especially when screaming it during sex."

The only reaction this earns Dean is a slight tightening of Mr. Novak’s jaw. He takes in a calm breath before slowly telling Dean, "Twice last week. Three times this one, and it's only Wednesday. We're not even two weeks into school yet, _Mr. Winchester._ "

"Thanks for the stats, teach. I had forgotten."

"Why?"

"Why did I forget? Oh, well, that's probably a mixture of the beatings, the weed, and the-"

"Enough!" For the first time, Mr. Novak loses his cool. He slams his hand down on the center of his desk as he stands up to tower over Dean. Dean just smiles up at him like an invitation. "Tell me why you've been acting up like this, Dean. You were never well-behaved, but my records indicate that this is a new level."

Shrugging, Dean teases, "Maybe I'm enjoying detentions. That Mrs. Harvelle is quite the MILF."

Eyes narrowed, Mr. Novak speaks in an unsettling voice, “No, Mr. Winchester. I think you’re in need of more than detention.”

For the first time, Dean loses some of his confidence. "And - and what is that?"

"You're 18, correct?"

"Uh, yeah?"

"Good." Mr. Novak steps back from his desk. Staring Dean down, he undoes the buttons on his cuffs and rolls up the sleeves of his dress shirt. Then he's slowly removing his tie, sneering when he sees the way Dean watches his fingers manipulate the silk in a trance. "Stand up, Dean."

For the first time in perhaps ever, Dean is speechless. He doesn't even realize he's following the order and standing until he's being beckoned forward. Dean stares at his feet as they move around the desk, only pausing when they've stopped so Dean is only inches from Mr. Novak. 

Dean stares up at him in both fear and curiosity. "Since you can't ever keep your mouth shut, I thought I'd help you out."

Before Dean can ask what he means, the silk of Mr. Novak's tie is brushing against his cheek. The man steps into his space further as he reaches behind Dean's head. That's when Dean realizes what's happening. Mr. Novak is tying his tie around Dean's head, letting the material slip between Dean's parted lips. He whimpers when Mr. Novak harshly tugs at the material so it's digging into the corners of his mouth. His body begins to tremble as the knot is firmly tied at the back of his head. 

Rolling his tongue against the material, Dean's surprised at how full his mouth feels despite the tie being thin. He tries to speak but only manages a muffled, incoherent, "Wa's 'oo do'n M's N'v?

Using his common sense, Castiel figures Dean is asking something along the lines of 'What's going on?' 

Castiel answers, not because he has to, but because he's not a dick. Even if Dean Winchester pushes every single one of his fucking buttons, he's not a dick. “I’m going to punish you properly.”

Castiel turns him so he's facing the desk, then rests his lips against the shell of Dean's ear. He chuckles when the boy shudders and presses back against him. "I think you're in need of something much more _hands on_ than detention, don't you think Mr. Winchester?"

Dean frantically nods, looking over his shoulder at Castiel with wide green eyes. 

"I think naughty boys like you need a lesson." He presses a hand to the middle of Dean's back, pushing until his front is resting against the desk. "I know why you keep getting sent here, Dean. I saw that look in your eyes the first time you saw me. You have a crush on the new principal."

Dean half-heartedly mumbles into his gag, shaking his head. This just makes Castiel laugh. "Don't lie. Liars are extra naughty. You don't want the extra naughty boy punishment now, do you?"

A slight whine escapes the boy as he quickly jerks his head in a firm no. "That's what I thought." 

Castiel can’t help but grin at the confirmation that this boy has a crush on him. It makes all his dirty thoughts regarding Dean the past two weeks much more valid. Just because he has a crush, though, doesn’t mean Dean wants it to be reality. Castiel knows if Dean starts to fight or begs to stop, this will be over in an instant. Gagged or not, he won't rape anyone. He is silently praying Dean wants this too. He has to make sure, though. Dean has to be able to say no. 

Castiel reaches over and picks up his small rubber band ball. He places it in Dean's right hand before softly stroking his arm to comfort him. "You drop that and this is over. I promise. If you get scared. If you don't want this. If I go too far. Drop that ball and everything stops, okay?"

Dean weakly nods. 

"Drop it for me, Dean. Show me what a good boy you can be."

The ball drops immediately, bouncing off Castiel's leg. 

"Mmmm, such a good boy," he coos as he kneels to grab the ball. He places it again in Dean's hand, then presses a firm kiss to the boy's cheek that isn't resting against the cool surface of the desk. It earns him a soft smile. 

That smile won't be there much longer. 

"Now, I usually punish my subs with ten lashes. But you've been sent here three times already this week, so I think thirty is best." Dean whimpers but squeezes the ball tighter, refusing to let it go. 

When Castiel begins to pull down Dean’s jeans, Dean startles. They both freeze for a moment but then Dean lifts his ass in the air like an invitation, his hand still firmly holding the ball, and Castiel continues.

Once Dean’s jeans are down to the middle of his thighs, Castiel runs a hand over the boy’s black lace panties. “Well, what do we have here?”

Dean whimpers, the noise turning into a low groan when Castiel takes both lace covered ass cheeks in his hands and squeezes hard. “I wonder what all your buddies would think if they found out Dean Winchester wears pretty panties. Should I tell them?”

Dean turns his head the best he can to look up at Castiel with wide, terrified eyes. He shakes his head frantically while begging Castiel through his gag not to tell. Castiel just chuckles. “I guess it can be our little secret. If you’re a good boy for me.”

With a nod of agreement, Dean rests his head back down on the desk and lifts his ass again, as if he’s telling Castiel that he’s ready to show him how good he can be. 

The sound of Castiel yanking his belt off makes Dean shiver. He jumps when the soft leather is dragged from one ass cheek to the other. Even through the panties, it feels amazing, making Dean’s body erupts with goosebumps. His skin feels like it’s on fire. It only gets worse when his panties are removed painstakingly slowly, the fabric whispering against him in the best way. 

Once his ass is exposed, Castiel folds the belt in half and starts to drag it back and forth again. Every few seconds, Dean tenses like he’s preparing himself for a hit. Eventually his body completely relaxes, though. He even finds himself humming. The sensation is nice. Like someone’s tickling him and -

_Oh fuck_. The first crack of the belt is so loud that Dean jumps from it more than the actual pain. He lifts his head slightly, looking at the door. Surely Mr. Novak knows they have to be quiet. They’re at school. In the middle of the day. 

Dean doesn’t have time to worry about it. Not when the blows start raining down so fast he’s unsure how Mr. Novak can even keep count. By the time the belt stops striking him, Dean’s ass feels like it’s been set on fire. It throbs with the beat of his heart and he finds himself reaching back with a hand, wanting to rub away the pain. 

“No no no. None of that,” Castiel chides, grabbing Dean’s hand before he can get to his destination. He collects Dean’s other hand as well and presses them together, using his belt to secure them above the boy’s head. “There we go. You still have five left, but I guess I’ll just have to use my hand for those.”

A tear leaks out of Dean’s right eye as he wonders if he can take much more. He still has the ball in one of his hands. Part of him wants to drop it. The other part thinks he’s strong enough to take this. He wants to be good. Not just for the whole panties secret, but for Mr. Novak in general. Dean wants more than anything to be Mr. Novak’s good boy. He needs to be. 

Castiel is a good dominant. He knows exactly what Dean is thinking. With one hand, he gently guides Dean’s face until their eyes are locked. Castiel’s other hand starts to stroke soothing circles on his abused ass cheeks. Dean hums in appreciation, looking up at Castiel with vulnerable eyes. 

“You’re being so good for me, Dean. Such a good boy.” Every muscle in Dean’s body relaxes, and he releases a soft sigh of relief. Castiel smiles. “Can you keep being good for me? For five more spankings?”

Dean nods. “Good boy.”

Before Dean can prepare himself, Castiel stands up straight again and lifts his hand. He spanks Dean once on his right cheek, then on his left. The boy squirms and whimpers, but he’s still squeezing the ball tight. Deciding to test Dean with his final three spankings, interested to see what the boy can take, Castiel lets himself loose. The first slap is his left, then on his right, then right over his crease so both cheeks are abused. Each hit was harder than Castiel thought he had in him, making his hands itch and vibrate with pain. His handprints are bright red over the already deep pink skin of Dean’s ass cheeks. When he looks up at the boy, he sees he’s quietly crying. 

Castiel releases Dean’s hands as he whispers softly, “That’s it, Dean. You’re a good boy. Such a good boy for me.” 

When the tie is removed from Dean’s mouth, he sniffles and licks his lips. He tries to thank Mr. Novak, but his voice cracks and breaks. 

With soft hands, Castiel guides Dean off the desk and turns him around. When they’re face to face, Castiel wipes Dean’s cheeks clean and smiles at him. Dean relaxes, smiling back. 

“Does my good boy want a reward?”

Dean’s eyes light up. “Yes.”

“Yes please, sir,” Castiel corrects, raising an eyebrow. 

With a shiver, Dean echoes back, “Yes please, sir.”

“On your knees.”

“Oh-” Dean pauses, feeling unsure. That doesn’t sound like a reward. He trusts Mr. Novak, though. He has no fucking idea why, but he does. It’s something in those blue eyes. They’re gentle, even when Mr. Novak is pissed off and yelling at him. Even when he was spanking him moments ago. Mr. Novak looks at Dean like Dean’s precious. Dean likes that. 

Castiel’s shocked when Dean says nothing more, and silently sinks to his knees without complaint. 

“Now, earlier you said there’s a difference between a blowjob and sex.” Castiel reaches down, cupping Dean’s right cheek and stroking a thumb over his pretty pink lips. “You offered to show me. I think I’ll give you the chance now.”

A beautiful blush spreads from Dean’s neck to the tips of his ears. He looks at Mr. Novak’s crotch where his erection is clearly trying to escape the confines of his dress pants, then flicks his gaze back up at him. 

“What do you say, Mr. Winchester? You want to show me?”

“Yes.” When Dean sees Mr. Novak raise an eyebrow, he quickly corrects himself. “Yes, sir. Please let me show you.”

“Good boy.”

The praise makes Dean shiver, his pupils dilating and his lips parting as he sucks in a sharp breath. It makes Castiel grin ear to ear. He knew Dean was a needy, submissive bottom just waiting to be tugged out from under the badass exterior he shows everyone else. He never thought Dean would be such a great submissive though. 

Castiel wants to keep him. Especially when he feels Dean’s nervous hands gently tugging his zipper down, green eyes flicking up at him to ask silent permission. Castiel cards his fingers through Dean’s hair and smiles down at him. “Go ahead, baby. Take it out.”

With an eagerness that Castiel knows would embarrass Dean if the boy wasn’t so turned on, he pulls at Castiel’s pants and boxers until his cock is springing free. Dean licks his lips and adjusts his knees so he’s at the perfect height. When Castiel’s cockhead is less than an inch from Dean’s mouth, he’s once again given big green eyes asking permission. 

Instead of verbally telling Dean to suck him, Castiel just tightens his hand in Dean’s hair to hold him still and uses his other hand to hold his cock steady as he guides it to Dean’s mouth. Dean opens for him immediately, but Castiel spends a few seconds just rubbing his leaking tip along Dean’s lips until they’re glistening with precum. 

“Look at you. So needy. So eager. But so patient and good for me.” Dean’s lips twitch into a slight smile, his eyes widening in a hopeful happiness. “I bet I could just jack myself right here, like this. Come all over your pretty little face. You wouldn’t even care, would you?”

“No, sir,” Dean admits in a husky whisper, his breath falling on Castiel’s cock and making him groan. 

“You’d probably even like it, wouldn’t you? To be covered in my cum? To be marked as mine?”

Dean nods rapidly. “Yes. Yes, sir. Yours.”

Castiel’s knees start to weaken, and he has to remind himself to get his shit together. This is a teenage boy. Eighteen or not. He’s a fucking student. He can’t be Castiel’s. This has to be a one time thing. 

“Suck my cock, then,” Castiel finds himself saying, even though he knows how wrong it is. Even though he never planned to take it this far. “Show me how much you want to be mine.”

With a soft whimper, Dean’s diving in and swallowing him down. The boy’s done this before. He’s good at it. The perfect amount of suction, bobbing, and tongue. When Castiel bucks his hips, pushing his cock further down Dean’s throat, the boy gags but takes it. When Dean begins to bob again, he makes sure the cock goes that deep every time, wanting to show Mr. Novak that he cares about his pleasure. Wanting to prove how good he can be. 

That’s when Castiel breaks completely. He grabs two fistfuls of Dean’s hair and holds him still as he begins to snap his hips forward fast and hard. Dean moans around his cock as drool leaks out the sides of his mouth. He just stares up at Castiel in awe as Castiel fucks his mouth. It’s his undoing. 

“Gonna come, baby.” He releases Dean’s head. “Pull away if you don’t want to swallow.”

Dean doesn’t move away. If anything, he gets closer, pushing Castiel down his throat until his balls are resting against Dean’s chin. Castiel spills down the boy’s throat with a few hot bursts of cum. Dean chokes and coughs, probably not prepared for what it would be like for the cum to be that deep in his throat as he tries to swallow, but he’s fine after a few seconds. 

Looking dazed, Dean blinks up at Mr. Novak through blurry eyes. He can feel his chin slick with spit, and possibly some cum. His cock is achingly hard and leaking a pool between his thighs, but he doesn’t care. He just wants to know if Mr. Novak is happy with him. 

Castiel gets on one knee in front of Dean, swiping a soft thumb along his chin to clean him up. When he puts the thumb to Dean’s lips in curiosity, he’s thrilled to find that Dean immediately takes it into his mouth and sucks it clean. 

Moaning, Castiel informs him, “You’re so fucking good. So good for me, Dean.”

“Thank you, sir.” Dean leans forward when Castiel starts to take his hand away, chasing his touch. When Castiel cups his cheek, Dean nuzzles it and sighs in relief, resting the weight of his head in Castiel’s palm. 

Yup. That’s it. Castiel is a goner. 

With his free hand, Castiel reaches down and gently tugs at Dean’s cock. Dean whimpers and leans further into Castiel’s touch, wiggling his hips a little to gain more friction. It’s not long before Castiel is spitting on his hand and picking up the pace, pulling filthy, beautiful sounds from Dean. 

“Gonna - gonna,” Dean breathes, unable to finish. 

“Go ahead. Come for me.”

Just seconds later, Castiel’s fingers are being covered with cum. Before Dean’s done spilling over his principal’s hand, before Castiel can pull away, Dean’s launching forward and crashing their lips together in a violent, hurried kiss. 

He immediately apologizes when Mr. Novak pulls away. “I’m sorry. That was bad. I’m so sorry, sir. I shouldn’t have-”

“Hush,” Castiel whispers, placing a finger over Dean’s lips to quiet him. The boy listens, but deflates. “You did nothing wrong. Thank you for kissing me. I like it very much.”

This makes Dean perk up, his cheeks flushing. He even gets the courage to ask, “Can I ever kiss you again?”

With a soft laugh, Castiel helps Dean to his feet and begins wiping his hand and Dean’s cock off with tissues. When Dean’s clean enough, Castiel pulls his panties and jeans back up, zipping and buttoning them for the boy. 

His boy. 

He may be going to hell, but he’s keeping this one. If Dean wants to be kept. 

“Sir?” Dean whispers, his voice trembling as he peers up at Castiel through his lashes. 

Castiel kisses Dean’s forehead, then says, “You can kiss me again, Dean. Soon. If you want to be mine.”

“Like your boyfriend?”

“In a way.” Castiel looks at Dean, searching his eyes for hesitation or fear. There isn’t any. “Do you know what it means to be a submissive, Dean?”

“Like Fifty Shades of Grey?”

This makes Castiel roll his eyes. “Not at all, but that’s a start I guess. I want you to do some research for me. Due tomorrow. I’ll be expecting you before classes start in the morning to discuss this.”

“I don’t need to,” Dean blurts. “I want to do that. I want to be yours.”

“Dean-”

“I’ll do the research. I’ll do whatever you want. But I’m telling you now, I won’t change my mind. I want this. I’ve never,” Dean pauses, glancing down at his feet and tangling his fingers together. Castiel doesn’t understand why he’s suddenly so nervous until Dean mutters, “I’ve never felt like that before. It was like I was floating. It was - I dunno. Safe, I guess. That’s stupid. I’m sorry. I’m so stupid. Just forget-”

“No, Dean. None of that. You are far from stupid.” Castiel grabs the boy’s face and forces Dean to lock eyes with him. “I’m glad you felt that way. I’ll make you feel that way for as long as you’ll have me. But do the research tonight so when we talk tomorrow, you understand what I’m saying. Understood?”

Dean nods. “Yes, sir.”

“Now go to class.”

“Yes, sir.” 

Dean takes a few steps away from him, heading toward the door, and Castiel’s fingers itch to touch him again. It’s like he’s addicted.

"Hey," Castiel says softly, grabbing Dean's hand and tugging him into his arms for a gentle embrace. "Next time you feel like misbehaving, you're coming to my house. I'll put you in my playroom and show you a real punishment."

Dean shivers before peeking up at Castiel through his eye lashes. "What if I want to be in your playroom, though?" 

"Then behave. Trust me Dean, the playroom is much more fun as a reward."

"Okay." Dean gulps, cheeks flushed bright red. He nods frantically. "Yes. Okay. Best behavior, sir. I promise."

"Yeah," Castiel says with a soft laugh. "We'll see."


	2. An Excellent Teacher

**Summary for the Chapter:**

> Ask & you shall receive - this is for all of you who loved More Than Detention so much! Here's a follow-up chapter (:

**Notes for the Chapter:**

> Bit of a time jump here (about a month)

When Mr. Shurley hands Dean his graded exam as he walks by his desk, Dean’s breath catches. He feels tears threatening his eyes and quickly blinks them away, slipping back into his usual mask. This is his last class of the day. He just has to make it seventeen more minutes. 

Those seventeen minutes are the slowest in human fucking existence if you ask Dean. 

Finally, the bell rings. Dean nearly sprints out of the classroom and down the hall. He stuffs his books that he needs into his backpack and slings the bag over his shoulder. Rushing through over to the freshman hall, Dean finds Sam talking with Gabriel and yanks him back. 

“Hey!” Gabriel yells, giving Dean a dirty look. 

“Shut up. You can kiss my little brother in a second.” Dean puts a twenty in Sam’s hand and looks him in the eye. “I’m not gonna be home until late. Buy you and Gabe some pizza, and don’t do anything I wouldn’t do.”

“Is there anything you wouldn’t do, Dean?” Sam teases as he pockets the cash. 

“Shut up.” Dean messes Sam’s hair up and winks at him. His smile slips a little when he remembers what he always needs to remind Sam about. “Call me if he comes home drunk, okay? I’m serious Sam.”

Sam nods. “I know, Dean. I’ll call. You just go do whatever the hell it is you’ve been doing the last month.”

“Trust me, I plan on it.”

As he runs away from them, he hears Sam say something about Dean’s sex life and him being gross. He knows it bothers Sam that Dean can’t tell him who he’s been secretly seeing, but it’s better this way. Castiel is putting enough on the line already. Dean doesn’t need to put him in any more danger. 

Speaking of Castiel, Dean finally reaches the door to the new principal’s office. He’s just about to walk inside when he’s stopped with a hand firm on his shoulder. Without needing to turn and look, Dean knows it’s his dominant. Every muscle in his body relaxes and the panicked feeling of finding Castiel is replaced with that warm safety he always feels in his presence. 

“I have parents in there, Dean. What do you need?” Castiel whispers. 

Instead of answering, Dean lifts his exam up in the air to show Castiel. His dominant growls - literally growls - and Dean feels him harden where he’s pressed up against Dean’s body. 

Even though Dean knows Castiel wouldn’t forget, he decides to remind his dominant of their deal. “Got a 99. You said anything over 90 got a reward.”

“Oh trust me, baby. You’re gonna be rewarded.” Castiel steps in closer and rests his lips on the shell of Dean’s ear, making Dean shiver. “You will use your key to get in my house. I want you to shower and eat the snack I have set out for you on the island. Then you will strip and fold your clothes as usual. You will kneel where you are supposed to kneel. And you will wait. Understood?”

“Yes, sir.” Dean licks his lips. “Do you want me prepped and plugged?”

“Where’s the fun in that? Tonight I plan on taking my time.” Dean shivers and nods quickly to show he understands. When he feels Castiel’s hand rest on the dip of his hip, Dean jumps. His breathing starts to pick up. Castiel just makes it worse by running the palm of his hand over the front of Dean’s jeans. “I’m so proud of you, baby. Now go be a good boy and do as told.”

  
  
  


\----

When Castiel gets home, he removes his coat and puts down his briefcase. He methodically works through his routine. He opens and reads the mail, then checks to make sure Dean ate his snack and cleaned up after himself. Castiel shrugs out of his suit jacket, loosens his tie, and rolls up his sleeves. He pre-heats the oven and preps the vegetables. Makes sauce on the stove. Drinks a small glass of wine. Puts the roast in the oven. 

Thirty-three minutes have passed since Castiel saw Dean at the school. If his calculations are correct, Dean’s probably been in the playroom for fifteen to twenty minutes now. It’s the longest he’s ever made Dean sit and wait in the playroom. He’ll be making it worth it, though. 

So. Damn. Worth. It. 

Castiel lets himself into the playroom, smirking when he sees the way Dean’s body perks up at his arrival. The boy continues to stay in his kneeling position on the soft cushion beside the doorway, every inch of him perfectly in place; ass settled on his feet, knees spread so his hard cock is on display, arms behind his back, one hand clasped on the opposite wrist, both hands settling at the small of Dean’s back. His head is bowed, chin tucked, eyes on the ground. 

Even from where Castiel stands a foot or two away, hovering above him, he can see that Dean’s entire body is covered in goosebumps. 

“99 on your Trigonometry exam,” Castiel muses, unable to keep from smiling. He can act all cold and dominating right now in the playroom, that’s fine, but in reality he’s fucking thrilled. Dean spent every night for the last two weeks studying for that exam. He met with Mr. Shurley two seperate times to get extra help. Castiel can’t wait to reward his beautiful boy for all that hard work. 

First things first, though. Castiel wants to use his pretty little submissive. 

Castiel grabs Dean’s cell phone from where they have agreed to put it during scenes - on top of the wooden dresser to the left where Castiel keeps the plugs and dildos. He checks to make sure Sam hasn’t reached out to Dean at all, then turns it on vibrate and slips it into his pocket so he’ll know if Sam does so. Then he grabs a chair and pulls it in front of Dean, taking a seat and leaning back in it. He can tell how hard Dean’s fighting not to look up at him. The boy stares intently at Castiel’s dress shoes, his muscles shaking from how much effort it takes to behave. 

“Look at me, Dean.” Green eyes immediately snap up, locking onto Castiel in relief. “I am so very proud of you, baby.”

Dean’s cheeks turn pink. “Thank you, sir.”

“Now I have my own plans for tonight, but I think you’ve earned a little say in the matter, don’t you?”

“Yes please, sir!” Dean says eagerly, leaning slightly forward. 

Castiel places the toe of his dress shoe against Dean’s hard cock and pushes gently - not enough to hurt him, but enough to remind him he could if he wanted to. “Get back in position, pet.”

“Sorry, sir,” Dean whispers, hurrying to adjust his weight. “C - can I still get a say, sir?”

“Of course. But don’t go breaking rules today. Don’t even push boundaries. This isn’t an excuse to misbehave, Dean. You’ll earn yourself a punishment for when your reward is over.” Castiel puts his elbows on his knees and leans down, taking dean’s chin in one hand. He grips it tight and smirks. “You don’t want to ruin your nice reward with a punishment, do you boy?”

Dean shivers. “No, sir. I’ll be so good for you. Promise.”

“I know you will.” Castiel gives him a soft kiss. Before he pulls away, he pauses to rub the tips of their noses together. It makes Dean smile and relax. “You can pick one thing we do tonight, Dean. It can be anything you want. A position. A toy. An aftercare component. The choice is yours.” 

Recognizing the panic in Dean’s expression at the sudden choice he has to make, Castiel leans back in his chair and starts to unzip his pants. “You can think about it while I fuck your mouth.”

Dean visibly relaxes, a soft sigh escaping through his pink lips. He stays in position like he’s supposed to, tipping his head into place and opening his mouth. Being the perfect little slut for Castiel, Dean stays still and waits to be fed his dom’s cock. He even sticks his tongue out. 

Groaning, Castiel inches forward on the chair and grabs the back of Dean’s head. He guides the boy to his cock and lets his leaking tip rest against the soft center of his sub’s tongue. Dean whines, flicking his green eyes up to silently beg. He wants Castiel’s cock so damn bad. Castiel knows his boy hates to be teased. He’s such a cockslut, and a cumslut, and Castiel loves making Dean show it by doing things like this. 

This is a reward after all, though. Castiel shouldn’t make the boy beg. 

Well… he shouldn’t make him beg  _ too  _ much. 

“Go ahead, baby. Suck my cock.”

Dean jumps at the opportunity, shifting his weight and coming up on his knees to get a better angle. He enthusiastically sucks Castiel down, humming as he pushes his principal’s cock to the back of his throat. This is something they’ve been working on lately. Dean loves the feeling of choking on a cock - the lack of air making him feel a strange sense of safety instead of fear - but his gag reflex betrayed him. Now Castiel’s little cock slut has almost completely gotten rid of that pesky reaction. Castiel watches in amazement as Dean chokes himself as much as he can, nuzzling the hairs on Castiel’s soft skin above his cock. He hums and relaxes despite the fact that it’s been 44 seconds since he could breathe - Castiel always counts in his head. 

He pushes until fifty before grabbing a fistful of Dean’s hair and yanking him off. Dean gasps as he sucks in oxygen, tears falling down his cheeks. Castiel cradles his face and smiles down at him fondly. “So perfect for me.”

“Thank you, sir,” Dean says in a raspy voice. 

“Have you decided what you want to do yet?”

Dean’s entire face flushes red, making Castiel smirk. His boy can be so bashful sometimes. It’s adorable, considering how dirty and slutty he usually is in the playroom, and how rambunctious and confident Dean is everywhere else. It makes Castiel feel special in a way. He enjoys the fact that Dean Winchester only lets his guard down with him. 

Peering up at Castiel through his lashes, Dean whispers, “Can I stay the night?”

Castiel’s breath is knocked out of him. That’s not at all what he was expecting. Dean absolutely loves getting rimmed - he thought maybe the boy would request that. He’s also a huge fan of riding Castiel - that was another option Castiel was prepared for. There was a chance Dean would ask for a bath after their scene - his boy gets so sleepy and calm in their bubble baths after they play. Maybe Dean would even ask for a little bit of power in their scene, wanting to get a taste of dominance - Castiel would have let him. 

But this? A sleepover? 

A sleepover is something they’ve agreed cannot happen between them. For one, Dean has a father that might notice if he doesn’t come home - depending on how drunk John is when he stumbles in. Another issue is Dean needs to take care of Sam. Then there’s the fact that Castiel is his principal, and that step for some reason just feels so much bigger than what they do in the playroom. 

The real reason, though - the reason neither of them have ever said out loud - is that a sleepover means this is more than just sex. A sleepover means this is something real between them. A relationship. Love. 

Dean’s finally admitting out loud that he’s ready for that. 

Castiel waits for panic to overwhelm him. He waits for his mind to race, assuring him he’s not ready, ordering him to run while he can. None of that happens, though. All he can focus on is the image of waking up to Dean in the morning. How the sunlight would come through the window and catch the specks of gold in the boy’s messy hair. How Dean would give him a sleepy smile and cuddle into him, begging for five more minutes - because let’s be honest, Castiel knows for a fact Dean Winchester would not be a morning person. 

“It’s okay,” Dean whispers, eyes falling to the floor. “Just forget I asked. We can-”

“Stop Dean.” Castiel reaches out and places a finger to Dean’s soft lips. When their eyes lock, Castiel gives the boy an encouraging smile. “I would love to have you sleepover. I’m sorry I took so long to answer. To be honest, I was busy enjoying the idea.” 

Dean’s blush deepens. “Really?”

“Of course, Dean. I would love to have you in my bed. To have you in my home.” Castiel rubs the pad of his finger along the outside of Dean’s mouth. “You are wanted, Dean. _ I _ want you. Don’t ever doubt that.”

“But-”

“No.” Castiel presses a kiss over Dean’s lips, effectively silencing him. When he pulls back, he pushes his feelings aside and slips back into his full-dom mode. “You know what I want today, Dean?”

“No, sir.”

“I want your eyes on me. Always. No looking at the ground. No closing your eyes when things get too intense. Whenever I look at you, you better be looking back.”

A shiver runs through Dean’s body as he smiles. Castiel has to swallow a chuckle at how happy Dean looks. Dean thinks this will be easy.  _ How adorable.  _

Let’s up the ante. 

“You know what else I want today, Dean?”

“N - no, sir.”

Castiel smirks as he reaches down and slips his thumb between Dean’s lips, shoving it into the boy’s mouth. He moans when Dean begins to enthusiastically suck the digit, tongue massaging it like he would a cock. “I want to see how far I can push you. My beautiful boy. I can give you the best orgasm of your life, if you trust me.” 

Castiel shifts his hand, letting the thumb slip out of Dean’s mouth while simultaneously shoving two fingers into it. He smiles as Dean begins to suck on his fingers again. The boy has an oral fixation like crazy. 

“Do you trust me, Dean?” Castiel asks softly, locking their eyes together. 

Dean vigorously nods. 

Every time Castiel hears that - or see it in this case - he feels a rush. The same happens now. That power he has over Dean is nothing compared to the honor he feels when Dean offers up his trust like that. 

“I’m going to be edging you tonight, baby.” Castiel knows Dean has never done that before. He made Dean fill out a packet regarding his experience, as well as his hard and soft limits. Of course, the packet has already had a lot of changes done to it since then. Dean’s discovered that he actually enjoys most of his soft limits, and he’s even moved some of his hard limits to the soft section. They’ve also added something Dean thought he’d love to the hard limits section after a particularly rough session - Dean Winchester is not a fan of wax play. Not at all. That night was the first time Dean used his safe word. 

One of the only soft limits left to be explored is edging. When Castiel had asked why it was a soft limit, Dean had admitted with shame that he didn’t want Castiel to push him too far. He was worried Castiel didn’t know his body. Wouldn’t be able to tell when it’s time to drop the line. Dean’s biggest fear is using his safe word - they’re still working on him getting over that - but with that fear in mind, Dean hadn’t wanted to be put in a situation where he was likely to use it once he reached his limit. 

Keeping eye contact, Castiel slowly asks, “Are you okay with me edging you tonight, Dean?”

He slips his fingers from Dean’s mouth, smiling again as he watches the boy subconsciously chase them for a moment before realizing he needs to speak.

“Yes,” Dean pants. “I trust you, sir.”

“Good.” Still seeing a lingering uncertainty in Dean’s eyes, Castiel adds, “I promise you, Dean. It will be so worth it. You’ll feel euphoric when I finally let you come.”

Dean licks his lips and nods. “I’m ready, sir.”

“You’re sure?”

“Yes. Promise.” 

Castiel looks at him a final time before nodding in agreement. He gestures to the spanking bench in the corner with a wicked grin. “Go lay yourself out on your stomach over there. Legs spread, hole on display for me.”

Hurrying to obey, Dean nearly trips over himself on his way to the piece of furniture. Not standing up from his chair, Castiel calls out, “Excuse me, boy?”

Dean freezes where he is, not looking back. “Yes, sir?”

“I believe I said I want your eyes on me at all times.”

“Oh. Right. S - sorry, sir.” Dean slowly turns to face Castiel. His expression is one of confusion and slight worry. “I - how do I-?”

“You’re smart, Dean. Figure it out.” 

After a second of standing there stunned, Dean’s eyebrows smooth out and he carefully begins to walk backwards toward the spanking bench. Castiel remains silent, but gives Dean an encouraging smile to show him he’s pleased. The non-verbal praise sends a shiver through his boy. 

Gaining confidence, Dean gets to the bench and turns so his stomach can be pressed against it. The entire time, though, he keeps his eyes on Castiel by turning his head. Even as he settles himself in place, spreading his legs like he was told, he keeps his left cheek pressed firmly to the leather padding so he can keep looking at Castiel. 

Castiel tests his boy’s patience. He remains seated, just watching as Dean lays there open and ready for him. Not once does Dean takes his eyes off of Castiel, even as he starts to blush from Castiel’s unwavering attention. Even as he starts to tremble with need. Curious, Castiel checks his watch and makes a decision. Dean can wait there for two more minutes. Or, at least, the boy can try. 

  
  


\----

  
  


Dean is a whimpering mess, and Castiel isn’t even near him. Every second that passes makes it harder for Dean to keep looking at Castiel. It’s so demeaning and humiliating. His principal is just sitting there, a bored expression on his face, looking at Dean like he’s nothing more than a cheap piece of art in a waiting room. It’s making Dean’s cock feel painfully hard, and he’s aware he’s leaking precum onto the bench beneath him. He doesn’t care. He just knows his dominant wants Dean’s eyes to stay on him, and the rule in all scenes is not to speak unless spoken to. So here Dean lies, looking directly at Castiel, lips closed tight. 

He might die this way, but he’ll die making Castiel happy. 

After who knows how long - though Castiel probably does, because Dean noticed his principal checking his watch often while making Dean wait - Castiel finally stands up from the chair and casually strolls over to Dean. When Castiel is just a foot away from him, hands in his pockets as he peers down at him, Dean holds his breath. 

It takes a second, but then his principal is tilting his lips into a very satisfied, proud smile. “Look at how patient my sweet boy is. So good for me.” 

Dean exhales a shaky breath at the words s _ weet boy. _ Castiel has used pet names before - usually just baby - but this is a whole new level. It makes Dean feel special and loved. 

Which makes Dean blush a deep, dark red. His instinct is to hide his face in the crook of his arm but he remembers last second that he’s not allowed to look away from Castiel. He’s now realizing how hard that’s going to be. Dean can’t wait until Castiel is behind him, because then it will be physically impossible for Dean to keep his eyes on him. Then Dean will be free to squeeze his eyes shut and hide his face all he wants. 

“Can’t wait for you to show off more of that patience. Shall we set a timer? See how long you can go before coming?” 

Knowing it’s a rhetorical question, Dean does nothing but whine. His response pulls a soft, sexy laugh from Castiel. He watches as the man glances at his watch. “4:38 PM. Do you think you’ll make it to 5, sweet boy?”

Dean whimpers at that pet name again, nodding his head quickly even though he doesn’t think there’s a shot in hell he’ll make it that long. He wants so badly to please Castiel. To be his good boy. His  _ sweet boy _ . 

“Sounds like a plan.” Castiel grins as he turns to the nearest dresser. He pulls out a sleek black box-shaped object that Dean doesn’t recognize. It isn’t until it’s being placed just two feet in front of Dean’s face, right at eye level with him from where it’s set down on the toy shelf, that he realizes what it is. It’s a digital clock. The bright blue numbers against the black screen makes Dean squirm. 4:39 now. 5 is so far away. 

“Hmmm. Something’s missing,” Castiel muses. Dean shivers at the mischief in his dominant’s voice. Whatever is missing won’t be something that Dean will enjoy. Not one bit. 

Sure enough, Dean watches as Castiel walks to a closet he’s never seen the man open before. The second Castiel pulls out a tall mirror that can stand on its own, Dean’s stomach falls, his heart beginning to race. He isn’t going to get a break from staring at Castiel. His principal is going to make damn sure Dean can always be looking at him. 

And, in doing so, Dean will be stuck looking at himself. Watching as he becomes a needy, writhing mess. 

Dean’s never felt more embarrassed and turned on in all of his life as Castiel puts the mirror in place. 

“Let’s begin,” Castiel says in a low, growly voice that’s full of dirty promises. 

Before Dean has time to wonder what will happen first, he’s watching Castiel’s reflection dip down. Dean throws his head back and groans when he feels Castiel’s tongue pressing flat against him. The man licks him like a kitten. It’s infuriating. Just the softest little touches of wet warmth. Dean wants his hole to be fucked with that tongue. He needs  _ more _ . 

“Please - nghh sir, please!” 

“Please what?” Castiel taunts, his voice vibrating Dean’s hole. 

“More. Please, sir, more!”

“If you say so.” Castiel lifts his head, meeting Dean’s eyes in the mirror. “You’ll regret this.”

“Wh- ooooh!” Dean chokes on his question of why he’d regret asking for more, already getting an idea of the answer anyway. The feeling of Castiel’s tongue pressing past his resistant rim and licking inside of him sends shock waves of pleasure through him. The level of intensity increases when Castiel shifts the angle of his face, his stubble scratching over Dean’s sensitive perineum. 

There’s no way Dean’s going to make it to 5. 

Dean’s hole is so sloppy and wet from the rimjob that two of Castiel’s fingers slide into him easily. His entire body tenses at the sudden spark of heat that occurs when Castiel rubs the pads of those fingers against Dean’s prostate. 

“Oh - sir, please.”

“We’re just getting started, baby. Better control yourself.” The threat is punctuated by a third finger entering Dean, Castiel’s tongue returning to flick and rub along the stretched rim. The first tear of what Dean knows will be many slips down his cheek. Dean’s surprised he’s not sobbing yet. 

He earns a break for a few seconds while Castiel pulls his fingers out and reaches over to his cart of instruments nearby. Dean watches the mirror in anticipation. Will Castiel use a dildo on him? A vibrator? A prostate massager? 

_ God, please don’t be a prostate massager. _ Dean’s prostate is so oversensitive Castiel usually tries to avoid it during sex just to let the boy last longer. 

Sagging in relief when he sees the studded vibrator in Castiel’s hand, Dean lifts his ass in invitation and locks eyes with his dominant in the mirror. Castiel sneers at him. The look sends ice through Dean’s veins. 

“Why is someone so eager to have this in his ass, hmm?” Castiel lubes up the toy as he talks, eyes never leaving Dean’s. “You think this won’t drive you wild?”

Dean bites his bottom lip, suddenly unsure. He had just been so relieved it wasn’t a prostate massager. Vibrators don’t really do it for Dean. Sure, they feel good, but they’re never enough. Especially with his cock being untouched right now. A vibrator will be easy. Dean can make it to 5 with a vibrator. 

Then the vibrator is being pushed into his hole, stretching him further than the three fingers did, and Dean’s vision is blurring. Each stud is pushed slowly against his prostate in an agonizing pace that makes Dean’s toes wiggle. When the vibrator is seated into place, the largest stud is heavily settled against his prostate, each breath making it move just enough to send sparks through Dean’s gut. Dean begins to tremble. 

It’s not even turned on yet. He’s doomed. 

Dean finds himself staring at the clock to the left of the mirror. 4:44. Only six minutes have passed since they started. Yeah, there’s no way he’ll be able to make it. 

The sharp hiss of a riding crop comes down on Dean’s right ass cheek, making him yelp. He brings his eyes up to look at Castiel’s in the mirror, not understanding what he did wrong. His dominant is glaring at him. Even shaking his head in disappointment. “What are you looking at, boy?”

“The clock, sir,” Dean whispers in a tiny voice, cheeks burning. 

“Did I say I want your eyes on the clock tonight, or on me, Dean?”

“Y - you sir.” 

“So why were you looking at the clock?”

Dean releases a tiny sob as the vibrator is turned on. He squeezes his eyes shut, tears pouring over his cheeks. 

“Open your eyes,” Castiel growls, bringing the crop down twice on each ass cheek. When Dean does as told, looking at the reflection of Castiel’s angry face in the mirror, Castiel does  _ something  _ that makes the vibrations gain speed and power. “That clock is for me, little slut. You have two jobs. Don’t come. Don’t stop looking at me. Understood?”

“Yes, sir,” Dean pants.

“Good boy.” Castiel turns the vibrator up again. If Dean could concentrate enough, he’d ask how the hell the thing could get any more intense. Not that it matters how. All he knows is that it’s happening. A warmth begins to curl inside his stomach, tendrils rushing through the rest of his body until every inch is vibrating along with the toy. He’s dripping sweat and crying harder. 

“Gonna come!” he shouts, feeling panicked. He wants to be good. He wants to be so so good. 

The vibrator is turned off, but left in place. A soft hand rests on the small of Dean’s back and begins stroking soothing circles there. Dean rests his chin on the bench, staring up at his principal’s reflection in amazement as his body slowly comes back from the edge. 

With a simple, “Again,” Castiel is switching the vibrator back on. The smirk he has on his face while watching Dean makes Dean even more turned on. He starts to hump against the bench, relieved when he realizes his cock is in the perfect spot to be rubbed between his stomach and the leather. It feels phenomenal. 

A tight fist grabs the back of his hair. Castiel yanks Dean up off the bench until he’s nearly bent in half, his back plastered to Castiel’s front. The new angle makes the vibrator jostle and rub against his prostate in an overwhelming way. Dean tries to move his hips so he can get friction, but all there is for his cock to feel is air. 

“Please - please, sir. Please. Need more. Need to come!”

“No, no. We can’t have that.” Castiel wraps a strong arm around Dean’s waist and picks him up, using his other arm to support his ass. Dean feels like a child as he’s carried to the bed - except it’s a much different experience, considering the toy continuously vibrating in his ass. “Naughty boy trying to rub yourself on my bench. Who told you that you could do that, slut?”

Dean whimpers. “N - no one, sir. ‘M sor - sorry, sir!”

“You aren’t yet. You will be.” Castiel lays Dean out on the bed, then slowly backs away from him. “Don’t move an inch, or you won’t come at all tonight.”

Holding his breath, Dean forces himself to stay completely still as he waits for his principal to come back. He groans when he sees that Castiel is carrying the mirror, now settling it at the foot of the bed. The clock is placed on top of a stool Castiel drags over. When he sees the red silk rope and leather cuffs in Castiel’s hands, Dean shivers. He looks up at Castiel’s face to see if he caught the movement. He either didn’t, or has decided to take mercy on Dean. 

_ Thank god. _

“Since I can’t trust you not to be naughty with your cock, I suppose I’ll just have to make it so you have no access to it.” Castiel removes his belt and unzips his pants, chuckling when he catches Dean licking his lips in anticipation. Keeping his pants and shirt on, Castiel climbs onto the bed near Dean’s head and lifts Dean into a sitting position. He holds still the best he can as Castiel moves him like a ragdoll into his lap, the vibrator thankfully taken out of his ass. 

Dean looks at the mirror just in time to see Castiel line his cock up at the base of his hole. He gasps at the realization he’s about to get fucked, the noise barely out before Dean’s principal is yanking Dean down hard and fast, burying himself completely inside his student. 

“Please!” Dean yells out, trying to lift his hips to ride Castiel. “Please fuck me, sir.”

Ignoring him, Castiel grabs Dean’s right wrist and puts the leather cuff on it, making sure it’s nice and tight. He does it again with the left. Dean watches in a trance as Castiel expertly weaves the red rope through the rings of the cuffs, then around the metal hooks on the bed posts. He pulls until Dean’s arms are straight out and up in the air at an angle before securing the two ends of the ropes together. 

When Dean wiggles, testing his new restraints, Castiel makes a tsking sound and wraps the ends of the rope he had secured together around Dean’s throat. He ties a loose knot there and smirks at Dean. “Go ahead. Move.”

Feeling like it’s a trick, Dean moves subtly to the left, testing his right wrist’s restraint. There’s an immediate tightening around his throat that starts to cut off his air supply, only going away when he’s back to sitting straight up. He looks in the mirror at Castiel with wide eyes. 

Castiel chuckles. “Don’t worry. You can be moved up and down just fine. Wanna see?” Without waiting for a response to his rhetorical question, Castiel grabs Dean’s hips and begins to violently fuck up into him. He was right. As long as Dean’s not moving from side to side, the rope on his neck is nothing more than a rough reminder of his lack of power. His cock bobs helplessly in the air with each thrust of Castiel beneath him. The break while the cuffs and rope were put on him was nice, but it wasn’t enough. Within minutes, Dean is teetering on that edge again. 

“Please let me come. I needa come, sir. Fuck - please.” Dean screeches when Castiel reaches up to harshly twist his left nipple. He tries to buck away but all that happens is he impales himself harder on Castiel’s cock while also choking himself on the rope. He releases a wrecked sob and apologizes. “Sorry, sir! Sorry for swearing! ‘M so sorry!”

“So disrespectful. Here I am spoiling you. Giving you a reward. And not only do you not behave or listen, but you swear too? In my playroom?” Castiel clicks his tongue. “You’re awfully close to earning that punishment.”

Dean tries to hang his head, stopping when he realizes that’s also going to choke him. He’s forced to stare Castiel straight in the eyes as he’s scolded. 

“So sorry, sir,” Dean whimpers. “S - ‘m sorry!”

  
  


“I know you are. My good boy. Don’t worry.” Castiel presses a soft kiss to Dean’s right shoulder. The gentle touch and the kind words are all it takes to have Dean right at the edge again. Castiel knows that, too. He knows what feeling loved does to Dean. It wrecks him more than any toy can. 

“Gonna!” Dean warns. He kicks his legs out in pain when a hand comes around his balls - not too tight, but tight enough to stop the orgasm that was surging forward. “No! No - please please please-”

“It’s not 5 yet, sweet boy. It’s only 4:51.”

Dean sobs openly now, not caring how broken and weak he sounds. He starts to shake his head. The safe word is at the tip of his tongue, but he bites it off and swallows it down. He can do this. Nine minutes. Dean can do anything for nine minutes. 

Detention. Studying. Watching ballet. Getting his ass kicked by his dad. 

Dean’s a survivor. 

He starts to doubt that when Castiel’s large hand wraps around his cock. At some point, he had lubed it up. Dean’s so out of it he hadn’t noticed. 

As he slicks Dean’s cock up with a steady pressure, Castiel begins nipping at his neck and shoulder. He leaves behind a trail of bruises like he always does - just beneath Dean’s collar, so he won’t be asked questions at school. 

“So beautiful for me, Dean,” Castiel whispers, moving inside him again while the hand on his cock continues its torture. “So sweet. So good. Look at you, baby. So close to the end. Been so good for me.”

Dean sobs again, screwing his eyes shut. He tilts his head back to rest it on Castiel’s shoulder and whimpers when the rope there chokes him for the effort. It magically disappears - Dean doesn’t care how - as does the pressure on his arms. He’s able to let his arms fall to the bed, though when he tries to bring a hand to his cock there’s still too much resistance somehow. If he had the energy, he’d open his eyes to see what Castiel has done to change these things. Honestly, though, he doesn’t give a fuck in the moment. 

“Please,” Dean whispers, tilting his hips as he greedily fucks back on Castiel’s cock. “Need to come so bad. S’ s’ ba’. Sir. Ple’ lemme. Lemme c’, sir!”

Castiel tsks, “You’re like a broken record.” There’s amusement in his voice, though. When Dean takes the chance and opens his eyes, he’s met with the sight of Castiel watching his reflection in the mirror like he’s a fucking work of art. It embarrasses Dean so he immediately closes his eyes again. 

That doesn’t stop Castiel from narrating the scene for him. “You have such a beautiful body, Dean. All this skin - scarred and flawed and freckled. These gorgeous nipples,” he tweaks each one, sending a rush to Dean’s head that makes him dizzy. 

“Pl - needa,” Dean pants.

“No.” Castiel stops moving inside him again, letting go of his cock at the same time. He continues talking like nothing happened. “God, and I love these tattoos on you. I could trace them for hours. And your face. All flushed and sweaty. You look wrecked, Dean. You should really open your eyes. Pretty pink lips puffy from me fucking you mouth earlier. Cheeks soaked in tears. Eyelashes clumped. Look at yourself, Dean.”

Unable to form words anymore, Dean just shakes his head in a firm no. 

“Dean, the rule is to look at me.” The tone of Castiel’s voice leaves no room for argument. Dean’s reached his principal’s limit. 

Whimpering, Dean snaps his eyes open to look at Castiel in the mirror. Looking at himself is unavoidable. He tries to hurry his focus back toward Castiel, but his dominant takes his chin and firmly tugs it. “No. Look at yourself now. Look at yourself while I fuck you to the edge.”

Dean shakes his head, whispering, “No, no, no,” under his breath as Castiel adjusts their position with one fluid movement, making it so Dean’s tilted forward and Castiel is on his knees, able to pound into him mercilessly from behind. 

When Dean lets his head hang between his shoulders, Castiel grabs a fistful of his hair and yanks until Dean’s back is flush to Castiel’s chest. Dean’s arms stop where they run out of slack on the rope, making it so he’s dangling like a helpless scarecrow as he’s fucked relentlessly. 

“Two minutes,” Castiel taunts, wrapping the hand that’s not buried in Dean’s hair around Dean’s cock. “Can you last, Dean?”

Dean sobs. “No! I ca - I can’t. Ple - ooooooh ple-”

“No.” Castiel lets go of both his hair and his cock, letting Dean fall back to his hands and knees. “I’ll make you wait longer if you look away from that mirror, Mr. Winchester.”

The sound of his name being spoken like that in this moment does crazy things to Dean’s mind. That’s how Castiel talks to him in school. Cold. Detached. Unimpressed. Full of disdain and ready to chew his ass out in front of his friends. No one at that place would have any idea the principal was buried cock deep in Dean Winchester’s ass most nights. No way. Not with the constant feud going between them. 

Tapping into his reserve of energy, Dean gives Castiel a flirty grin and says, “Bring it, Novak.”

He’s not really willing to break the rule, though. He can’t look at the clock, but Dean knows he must not have more than a minute left now. No way in hell is he going to ruin that just to be a brat. He doesn’t care how he looks in that mirror. It doesn’t feel dirty or wrong like he expected. He doesn’t see himself as some whimpering, writhing little porn star twink. 

Dean sees himself as Castiel sees him. 

Wrecked. 

Beautiful. 

Perfect. 

“Come for me, sweet boy.”

Dean’s eyes flutter closed, and he’s gone. 

  
  


\----

  
  


Castiel's favorite part of playing with Dean is this; Dean floating in a peaceful happiness, muscles finally relaxed, the weight of the world lifted from his shoulders, lying in Castiel’s arms because he trusts the man to take care of him during the experience. Sure, they have amazing sex - Dean’s the best submissive Castiel has ever had - but with Dean it’s more. So much more. 

It shouldn’t be. The damn kid is his student. 

He’s head over heels in love. Dean can’t graduate soon enough, because all Castiel wants to do is collar him and keep him as his beautiful boyfriend and submissive. He doesn’t want to scare Dean away, so he hasn’t brought any of this up. That’s why he was so shocked - and so fucking happy - that Dean asked for a sleepover tonight. 

Castiel can’t stop smiling as he holds Dean in the playroom bed. He doesn’t have to jostle the boy awake and hurry through aftercare so he can get on home. Castiel doesn’t have to lay awake staring at his phone all night, worried sick Dean will drop and need him. Tonight, Castiel can fully appreciate his boy. Take care of him. Spoil him. Show him what life could maybe be like after this school year. 

Dean stirs in Castiel’s arms, mumbling under his breath. He arches his back and yawns. Castiel gently runs his fingertips along Dean’s back, waiting to see if Dean will decide to come back to reality now, or if he wants to drift away again. In case Dean’s worried about making the choice, Castiel whispers, “I’m right here, Dean. You’re safe. Take your time.”

After a tiny nuzzle where Dean’s nose rubs against Castiel’s neck, Dean releases a happy sigh and melts back into Castiel’s hold. The older man smiles to himself before planting a kiss to the crown of Dean’s head. 

“Take your time,” he repeats. “I’m not goin’ anywhere baby.”

It’s another twenty minutes before Dean starts to wake up again. Castiel spent the time gently rubbing the parts of his body where the rope had been, applying cream to his barely-pink butt where he got a few swats with the riding crop, and massaging his shoulders and back to relax him. 

“C - cas?” Dean croaks, slowly blinking his eyes. 

“Shhh. You’re okay. I’ve got you.” Castiel grabs Dean’s chin and tilts his face up so that, when his eyes finally manage to stay open, he’ll be looking right at Castiel. It takes a few more seconds but then he’s rewarded with hazy green eyes. “I’ve got you, Dean.”

“Cas,” Dean whines, bringing a hand up to wipe at his eyes. When he looks at Castiel again, his gaze is focused and clear. “W’ times it?”

“Just after six.” 

“Sam?” 

Castiel shakes his head. “Nothing from Sam. He’s okay.”

“Mmmm.” Dean lets his eyes close again, resting his cheek against Castiel’s chest. “Hungry.”

“The roast is in the oven. Should be done in a half-hour. Do you want to take a warm bath with me while we wait?”

“Mmmm - far ‘way.”

Chuckling, Castiel scoops Dean up and moves to the edge of the mattress. “I’ll carry you, spoiled brat.”

Dean blushes. “Notta brat.”

“You sure are. Don’t forget the first time we got together, sweet boy.” He kisses Dean’s forehead. “Don’t worry, though. I love spoiling my little brat. He deserves it.”

“Cas,” Dean grumbles, his face turning bright red. 

“Sorry. Sorry.” Castiel turns the low lighting on in the bathroom and sits Dean down on the closed toilet lid. “Ya know, one of these days you’re gonna believe me when I say those things. You’ll realize that you deserve the world, Dean.”

Dean ducks his head, saying nothing. Castiel leaves him be. He knows that pushing Dean on this subject area just makes the boy shut down. That’s the last thing he wants tonight. Instead, he focuses on starting the bath, making sure the water is at the perfect temperature; warm enough to soothe, but cool enough not to burn Dean’s skin. 

After adding some of the lavender and melissa bath powder to the running water, Castiel strips out of his clothes. He checks Dean’s phone again before placing it on the counter beside the sink. Then he kneels in front of his boy that’s starting to look too zoned out for his liking and places his hands on Dean’s knees. 

“You still with me, baby?”

Dean closes his eyes for a few seconds before looking at Castiel and nodding once. “Sorry. Spaced out.”

“Can you tell me where your head went?”

Green eyes look away from Castiel, focusing on the bubbling bath water. “I got an A today.”

Castiel smiles softly. “Yes, I know. I’m so proud of you, Dean.”

“Cas.” Dean bites his bottom lip, stopping himself from saying more. 

“Please talk to me, Dean. You know how important it is to talk during this time.”

Nodding to show he understands, Dean wipes a stray tear off his cheek and sucks in a shaky breath. “Ya know, you’re the first person to ever expect good things from me. That’s why I found you so amusing. Ever since kindergarten, I’ve been the problem kid. Fist-fights, skipping school, not doing homework, mouthing off. No one cared about my living situation. No one cared I was practically raising Sammy on my own. I was just written off.” 

Dean releases a self-deprecating laugh before continuing. “You know what Mrs. Harvelle told me the first day of freshman year? She took one look at me and said _ ‘I’ve heard about you, Winchester. Just sit in the back and keep your mouth shut, and I’ll pass you with a D.’  _ That was how everyone was. People I hooked up with never expected a relationship - never even tried to bring the topic up. My teachers never ask me questions in class or even expect me to show up. Then senior year comes around, and this gorgeous man with kind eyes and a mischievous smirk calls me out on every fucking thing. I sneezed wrong, and I was in your office. At first I thought you just got a sick kick out of it, but you don’t, do you?”

“No, Dean. I didn’t enjoy punishing you like that.”

“How’d you know?”

Doing that little head tilt Dean’s always teasing him for, Castiel asks, “What do you mean?”

Dean gently touches his kneecap, tracing the little square shaped bone. “You were the first person to think I could be better. That there was more in me. How’d you know you were right?”

“The principal before me actually left me a note about you - attached to your file. A warning to keep my eye out for the school’s number one trouble maker.” Castiel reaches over, turning the water off before the tub overflows. “I watched you. You laughed a lot, but it sounded heavy. When no one was looking, you’d sometimes let your smile slip. Any time you flirted or kissed or messed around with someone, it almost looked like you were doing a chore. Going through the motions. Whenever you were late to class, it was because you were crossing the building to check on Sam during the three-minute break. In the time between the first day and the day in my office when we first got together, you walked around with four different books in your back pocket. Fahrenheit 451. To Kill A Mockingbird. The Little Prince. Howl.” 

Dean blushes. “I got an A today.”

“Yeah, Dean. You did.”

“I like who I am with you.”

“I’m pretty fond of that Dean myself.” Castiel cups his cheek. “That Dean seems happy.”

“He is.” Dean sniffles. “I am.”

“Then what’s got you looking like this? You’re clearly upset, baby.”

Dean fidgets, eyes darting to the bath in longing. “Besides Sammy, I’ve never had anyone I could lose. Anyone I loved enough to even care about losing. Not since my mom. But I was just sitting here, watching you start our bath, and I just - I can’t-” Dean peeks up at Castiel through his lashes. “I can’t lose you.”

Relief blooms in Castiel’s chest. That’s a problem he can handle. “You won’t, Dean. You won’t lose me.”

“How do I trust that?”

“You just do.” Castiel presses a soft kiss to Dean’s forehead before pulling him up to his feet. “You trusted me tonight. You’ve trusted me a lot recently. We’ve pushed all of your limits. Done things that scared you or made you nervous. You already trust me, Dean. You trust me with your body. Now you just have to trust me with your heart.”

Dean chuckles. “I’ve never been very good at doing that.”

“That’s fine.” Castiel winks at him. “I’m an excellent teacher.”

**Author's Note:**

> follow me on tumblr/send prompts @ destiel-love-forever


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